EP4284796B1 - Crystal form of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1h-1,2,4-triazol-3-yl)phenyl)amino)-n-(methyl-d3)pyridazine-3-carboxamide - Google Patents

Crystal form of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1h-1,2,4-triazol-3-yl)phenyl)amino)-n-(methyl-d3)pyridazine-3-carboxamide Download PDF

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Publication number
EP4284796B1
EP4284796B1 EP22704232.2A EP22704232A EP4284796B1 EP 4284796 B1 EP4284796 B1 EP 4284796B1 EP 22704232 A EP22704232 A EP 22704232A EP 4284796 B1 EP4284796 B1 EP 4284796B1
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European Patent Office
Prior art keywords
methyl
crystalline form
compound
cyclopropanecarboxamido
triazol
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EP22704232.2A
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German (de)
English (en)
French (fr)
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EP4284796A1 (en
Inventor
Victor W. Rosso
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Bristol Myers Squibb Co
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Bristol Myers Squibb Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Definitions

  • the present invention generally relates to a crystalline form of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)phenyl) amino)-N-(methyl-d 3 )pyridazine-3-carboxamide.
  • the present invention also generally relates to pharmaceutical compositions comprising the crystalline form, as well methods for obtaining such crystalline form.
  • the compound in a solid form that is physically and chemically stable upon storage, including at different conditions of temperature and humidity. It is also advantageous to provide the compound in a solid form that exhibits little loss upon storage, and low moisture uptake.
  • a powder X-ray diffraction (PXRD) pattern comprising" a number of peaks selected from a specified group of peaks, is intended to include PXRD patterns having additional peaks that are not included in the specified group of peaks.
  • a PXRD pattern comprising four or more, preferably five or more, 2 ⁇ values selected from: a, b, c, d, e, f, g, and h
  • a PXRD pattern having: (a) four or more, preferably five or more, 2 ⁇ values selected from: a, b, c, d, e, f, g, and h; and (b) zero or more peaks that are not one of peaks a, b, c, d, e, f, g, and h.
  • Forms of Compound (I) have been described in WO 2018/183656 (Form A), WO 2019/232138 (Form B), and WO 2020/251911 (Forms C and D).
  • the present invention generally relates to Form E of Compound (I).
  • Crystalline Form E of Compound (I) is characterized by unit cell parameters approximately equal to the following:
  • crystalline Form E of Compound (I) is characterized by (i) a powder X-ray diffraction pattern comprising 2 ⁇ values in degrees (CuK ⁇ ) at 9.0 ⁇ 0.2 and 11.3 ⁇ 0.2, wherein the PXRD pattern of Form E is measured at room temperature; and (ii) an endotherm with peak max in the approximate range of from 249 °C to 253 °C. In further embodiments, the endotherm peak max is at about 251 °C. It should be understood that, in some cases, the endothermic event may not be detected.
  • crystalline Form E of Compound (I) is characterized by an observed powder X-ray diffraction pattern substantially as shown in FIG. 1 .
  • crystalline Form E of Compound (I) is characterized by an endotherm peak max in the approximate range of from 249 °C to 253 °C. In further embodiments, the endotherm peak max is at about 251 °C.
  • the Form E of Compound (I) is substantially pure.
  • Form E of Compound (I) may be present in a sample at a purity of greater than 90 weight %, greater than 95 weight %, or greater than 99 weight %, while the remaining material comprises other form(s) of the compound and/or reaction impurities and/or processing impurities.
  • Seed crystals may be added to any crystallization mixture to promote crystallization. Seeding may be employed to control growth of a particular polymorph or to control the particle size distribution of the crystalline product. Accordingly, calculation of the amount of seeds needed depends on the size of the seed available and the desired size of an average product particle as described, for example, in " Programmed Cooling of Batch Crystallizers," J.W. Mullin and J. Nyvlt, Chemical Engineering Science, 1971,26, 369-377 . In general, seeds of small size are needed to effectively control the growth of crystals in the batch. Seeds of small size may be generated by sieving, milling, or micronizing of large crystals, or by micro-crystallization of solutions. Care should be taken that milling or micronizing of crystals does not result in any change in crystallinity from the desired crystal form (i.e., a change to amorphous or to another polymorph).
  • Form E of Compound (I) may be characterized using various techniques, the operation of which are well known to those of ordinary skill in the art.
  • Form E may be characterized and distinguished using single crystal X-ray diffraction, which is based on unit cell measurements of a single crystal at a fixed analytical temperature. A detailed description of unit cells is provided in Stout & Jensen, X-Ray Structure Determination: A Practical Guide, Macmillan Co., New York (1968), Chapter 3 .
  • the unique arrangement of atoms in spatial relation within the crystalline lattice may be characterized according to the observed fractional atomic coordinates.
  • Such methods include solid state nuclear magnetic resonance (ssNMR), differential scanning calorimetry (DSC), thermography, and gross examination of the crystalline or amorphous morphology. Two or more of these parameters may also be used in combination to characterize the subject form.
  • ssNMR solid state nuclear magnetic resonance
  • DSC differential scanning calorimetry
  • thermography thermography
  • gross examination of the crystalline or amorphous morphology Two or more of these parameters may also be used in combination to characterize the subject form.
  • the collected organic layer was diluted with MTBE (4.0 kg, 5.4 L/kg), washed with brine twice (25 wt%, 4.0 kg followed by 12 kg).
  • the organic layer was distilled under vacuum until total volume became approximately 10 L/kg.
  • Two put/take distillations with ACN (2 ⁇ 10 L/kg) were undertaken for the purpose of azeotropic drying.
  • the crude was cooled to 20 °C.
  • ACN (10.0 kg, 12.8 L/kg) and NaN(CHO) 2 (3.3 kg, 1.2 equiv.) were added.
  • the crude was heated to 65 °C and agitated until reaction reached completion.
  • DSC Differential scanning calorimetry
  • Moisture sorption isotherms were collected in a TA Instrument VTI-SA+ Vapor Sorption Analyzer using approximately 10 mg of sample. The sample was dried at 60 °C until the loss rate of 0.005 wt %/min was obtained for 10 minutes. The sample was tested at 25 °C and 4 or 5, 15, 25, 35, 45, 50, 65, 75, 85, and 95% RH (relative humidity). Equilibration at each RH was reached when the rate of 0.01 wt%/min for 35 minutes was achieved or a maximum of 600 minutes was reached.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Rheumatology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pain & Pain Management (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP22704232.2A 2021-01-29 2022-01-28 Crystal form of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1h-1,2,4-triazol-3-yl)phenyl)amino)-n-(methyl-d3)pyridazine-3-carboxamide Active EP4284796B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202163143769P 2021-01-29 2021-01-29
PCT/US2022/014261 WO2022165141A1 (en) 2021-01-29 2022-01-28 Crystal form of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1h-1,2,4-triazol-3-yl)phenyl)amino)-n-(methyl-d3)pyridazine-3-carboxamide

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EP4284796A1 EP4284796A1 (en) 2023-12-06
EP4284796B1 true EP4284796B1 (en) 2025-04-16

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EP22704232.2A Active EP4284796B1 (en) 2021-01-29 2022-01-28 Crystal form of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1h-1,2,4-triazol-3-yl)phenyl)amino)-n-(methyl-d3)pyridazine-3-carboxamide

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US (2) US12129245B2 (https=)
EP (1) EP4284796B1 (https=)
JP (1) JP2024505063A (https=)
KR (1) KR20230137962A (https=)
CN (1) CN116829549A (https=)
AU (1) AU2022214313A1 (https=)
CA (1) CA3206254A1 (https=)
ES (1) ES3026120T3 (https=)
IL (1) IL304597A (https=)
MX (1) MX2023008651A (https=)
WO (1) WO2022165141A1 (https=)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7113023B2 (ja) * 2017-03-30 2022-08-04 ブリストル－マイヤーズ スクイブ カンパニー ６－（シクロプロパンアミド）－４－（（２－メトキシ－３－（１－メチル－１ｈ－１，２，４－トリアゾール－３－イル）フェニル）アミノ）－ｎ－（メチル－ｄ３）ピリダジン－３－カルボキシアミドの製造方法
EP4387968B1 (en) * 2021-08-20 2025-11-12 Bristol-Myers Squibb Company Crystal forms of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1h-1,2,4-triazol-3-yl)phenyl)amino)-n-(methyl-d3)pyridazine-3-carboxamide
EP4423086A1 (en) 2021-10-25 2024-09-04 Kymera Therapeutics, Inc. Tyk2 degraders and uses thereof
CN116574056A (zh) * 2023-04-10 2023-08-11 五邑大学 一种氟代异喹啉酮类化合物的制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018183656A1 (en) 2017-03-30 2018-10-04 Bristol-Myers Squibb Company Crystal form of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1h-1,2,4-triazol-3-yl)phenyl)amino)-n-(methyl-d3) pyridazine-3-carboxamide
WO2019232138A1 (en) 2018-05-31 2019-12-05 Bristol-Myers Squibb Company Crystalline form of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1h-1,2,4-triazol-3-yl)phenyl)amino)-n-(methyl-d3) pyridazine-3-carboxamide
WO2020251911A1 (en) 2019-06-12 2020-12-17 Bristol-Myers Squibb Company Crystalline salt forms of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1h-1,2,4-triazol-3-yl)phenyl)amino)-n-(methyl-d3) pyridazine-3-carboxamide

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LT3495358T (lt) * 2012-11-08 2022-05-25 Bristol-Myers Squibb Company Amidais pakeisti heterocikliniai junginiai, naudingi kaip il-12, il-23 ir (arba) ifn alfa atsako moduliatoriai

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018183656A1 (en) 2017-03-30 2018-10-04 Bristol-Myers Squibb Company Crystal form of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1h-1,2,4-triazol-3-yl)phenyl)amino)-n-(methyl-d3) pyridazine-3-carboxamide
WO2019232138A1 (en) 2018-05-31 2019-12-05 Bristol-Myers Squibb Company Crystalline form of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1h-1,2,4-triazol-3-yl)phenyl)amino)-n-(methyl-d3) pyridazine-3-carboxamide
WO2020251911A1 (en) 2019-06-12 2020-12-17 Bristol-Myers Squibb Company Crystalline salt forms of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1h-1,2,4-triazol-3-yl)phenyl)amino)-n-(methyl-d3) pyridazine-3-carboxamide

Non-Patent Citations (4)

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Title
ANONYMOUS: "Crystalline form of Deucravacitinib", IP.COM; IPCOM000277367D, 14 January 2026 (2026-01-14), XP093361135
BURNETT DAN, ARMANDO R. GARCIA, MAJID NADERI, MANASWINI ACHARYA: "Moisture sorption properties of pharmaceutical materials studied by DVS (v1.0)", SURFACE MEASUREMENT SYSTEMS; DVS APPLICATION NOTE 101, 27 August 2015 (2015-08-27), XP093361138, Retrieved from the Internet <URL:https://public.jenck.com/notijenck/uploads/propiedades-de-sorcion-de-humedad-de-los-materiales-farmaceuticos-estudiados-por-dvs.pdf >
D5 - EUROPEAN PHARMACOPOEIA 6.0, 01/2008, "5.11. CHARACTERS SECTION IN MONOGRAPHS"
D7 - Q&A WITH ARDENA EXPERTS:DYNAMIC VAPOR SORPTION (DVS) AND ITS RELEVANCE IN API CHARACTERIZATION (2023/11) ACCESSED FROM HTTPS://ARDENA.COM/CONTENT/UPLOADS/2023/11/ARDENA_QA_DVS.PDF 14 JANUARY 2026 (NO DATE FOUND ON PAPER)

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US20250154132A1 (en) 2025-05-15
US12129245B2 (en) 2024-10-29
ES3026120T3 (en) 2025-06-10
JP2024505063A (ja) 2024-02-02
IL304597A (en) 2023-09-01
KR20230137962A (ko) 2023-10-05
CA3206254A1 (en) 2022-08-04
WO2022165141A1 (en) 2022-08-04
CN116829549A (zh) 2023-09-29
US20220259183A1 (en) 2022-08-18
MX2023008651A (es) 2023-08-01
AU2022214313A1 (en) 2023-08-17
EP4284796A1 (en) 2023-12-06

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